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Eyup Akgün

Education/Training
University of Marburg, Marburg, Germany, B.S. (Chemistry) University of Marburg, Marburg, Germany, M.S. (Organic Chemistry) University of Marburg, Marburg, Germany, Ph.D. (Medicinal Chemistry) Assoc. Prof. (registered Technical University of Istanbul) Faculty of no tenure tract of University of Pittsburgh; Pittsburgh, PA Faculty of no tenure tract, University Of Minnesota, MN
Employment
University of Ottawa; Ottawa, Canada
Medicinal Chemistry Post-doctoral University of Wurzburg; Wurzburg, Germany Scientific and Technical Council of Turkey; Gebze, Turkey Faculty of no tenure tract of University of Pittsburgh; Pittsburgh, PA Senior Scientist, Faculty of no tenure tract, University Of Minnesota Minneapolis Veteran Affairs (VA) Medical Center; Minneapolis, MN University of Minnesota, Dept. of Medicinal Chemistry; Minneapolis, MN Senior Research Associate, coordinator of project “Ligands that target opioid-chemokine and opioid-mGlu5 heteromers” University of Minnesota, Dept. of Medicinal Chemistry; Minneapolis, MN

HONORS AND MEMBERSHIPS
• Scientist of the year- 1987 (Sedat Simavi Foundation, Turkey) • Award for Cancer Research- 1990 (Wesley Foundation, Kansas) • Scholarship for Successful Foreign Student- 1972 (West Germany)
PUBLICATIONS
• Erin E. Cawston, Polo C. H. Lam, Kaleeckal G. Harikumar‡, Maoqing Dong, Alicja M. Ball, Mary Lou Augustine, Eyup Akgu¨n, Philip S. Portoghese, Andrew
Orry, Ruben Abagyan, Patrick M. Sexton, and Laurence J. Miller.
Molecular Basis for Binding and Subtype Selectivity o1,4-Benzodiazepine
Antagonist Ligands of the Cholecystokinin Receptor. Journal of Biological
chemistry, 2012, 287,pp(in press).
• Mario D. Aceto, Louis S. Harris, S. Stevens Negus, Matthew L. Banks, Larry D. Hughes, Eyup Akg¨un, and Philip S. Portoghese. MDAN-21: A Bivalent Opioid Ligand Containing mu-Agonist and Delta-Antagonist Pharmacophores and Its Effects in RhesusMonkeys. International journal of medicinal chemistry, 2012, (in press). • Harikumar, K.G.; Akgün, E.; Portoghese, P.S.; Miller, L.J. Modulation of Cell Surface Expression of Nonactivated Cholecystokinin Receptors Using Bivalent
Ligand-Induced Internalization. J.Med.Chem. 2010, 53: 2836-2842.
• Eyup Akgu¨n,‡,| Meike Ko¨rner,†,| Fan Gao,† Kaleeckal G. Harikumar,† Beatrice Waser,§ Jean Claude Reubi,*,§ Philip S. Portoghese,*,‡ and Laurence J. Miller*,
Synthesis and in Vitro Characterization of Radioiodinatable Benzodiazepines
Selective for Type
1 and Type 2 Cholecystokinin Receptors. J.Med.Chem. 2009, 52: 2138-2147.
• A Bivalent ligand (MDAN-21) containing µ-agonist and δ- antagonist pharmacophores is devoid of significance physical dependence capacity in rats. Aceto, M.D., Portoghese, P.S., Akgün, E., Harris, L.S. cpdd 2009, June 20-25, Reno/Sparks, Nevada Control.ID: 586278. • Induction of heterodimerization of mu opioid (MOP) and type B cholecystokinin (CCKB) receptors by bivalent ligands.
Zheng, Y.; Akgün, E.; Harikumar, K.G.; Hopson, Powers, M. D., Lunzer, M.M.,
J.; Miller, L.J.; Portoghese, P.S. J.Med.Chem. 2009, 52 (2), pp 247–258.
• Eyup Akgün, Yaguo Zheng, Kaleeckal G. Harikumar, Jessika Hopson, Laurence J. Miller, Philip S. Portoghese. Induction of heterodimerization of mu opioid peptide (MOP) and type-2 cholecystokinin (CCK2) receptor by novel bivalent ligands. Drugs Fut 2008, 33(Suppl. A): XXth Int Symp Med Chem (Aug31-Sept4, Vienna) 2008. • Synthesis and 124I-labeling of m-iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors
Akgün, E.;.; Portoghese, P.S.; Sajjad, M. Nabi, H.A. J.Labelled Comp.
Radiopharm., 2007, 50, 165-170.
• N1’-(p-[18F]Fluorobenzyl)naltrindole (p-[18F]BNTI) as a potential PET imaging agent for DOP receptors. Akgün, E.; Sajjad, M.; Portoghese, P.S. J.Labelled
Comp. Radiopharm., 2006, 49, 1-10.
• [C-11]NALTRIBEN: SYNTHESIS AND BIODISTRffiUTION OF A SELECTIVE δ2-OPIOID RECEPTOR ANTAGONIST FOR PET IMAGING.
M. Sajjad. C. D. Amett*, T. T. Conway, E. Akgun, and P. S. Portoghese**,
Eleventh international symposium on radiopharmaceuticals chemistry,
Vencouver, B.C. Canada, August 13-17, 1995
• “Synthesis of 123I and 125I-Labeled 5-Iodo-6-nitroquipazine." C. A. Mathis, J. D. Enas, S. M. Hanrahan and E. Akgün, J.Labelled Comp. Radiopharm., 1994, 34,
905.
• “Binding Potency of 6-Nitroquipazine Analogues for the Serotonin Reuptake Complex .” C. A. Mathis, S. E. Taylor, J. D. Enas and E. Akgün, The Journal
of Pharmacy and Pharmacology, 1994, 46, 751
• “Rapid Reduction of Sulfones to Sulfides Using LiA1H4/TiCl4.” E. Akgün, K. Mahmood and C. A. Mathis, J.C.S. Chem. Comm., 1994, 761. • “Galactose-Imines in the Staudinger Reaction.” G. I. Georg, E. Akgün, P.M. Mashawa, M. W. Milstead, H. Ping, Z. Wu, D. Vander Velde and F. Takusagawa, Tetrahedron Lett., 1992, 2111. • “Asymmetric Synthesis of β-Lactams and N-Benzoyl-3-phenylisoserines via the Staudinger Reaction.” G. I. Georg, P.M. Mashava and E. Akgün, M.W. Milstead, Tetrahedron Lett, 1991, 3151. • “Metal Directed Stereoselective Synthesis of 3-N,N’-Dimethyl-2-Azetidinones from α-N,N’-Dimethyl Glycine Esters.” G. I. Georg and E. Akgün, Tetrahedron Lett., 1991, 5521. • “Metal Directed Stereoselective Synthesis of 3-(1”-Hydroxyethyl)-2-azetidinones from Ethyl-3-hydroxybutyrate.” G. I. Georg and E. Akgün, Tetrahedron Lett., 1990, 3267. • “Reaction of Electron-rich Heterocycles with Electrophiles. Formylation of Indoles by Thiomethylation” E. Akgün and M. Tunali, J. Het. Chem., 1990, 27,
1473.
• “A Novel Synthesis of 2-Vinylindoles and their Utilization in the Diels-Alder Reaction for the Formation of new [c] Anellated Carbazole Derivatives.” E. Akgün and M. Tunali, J. Het. Chem., 1989, 26, 1869.
Diindolylantipyrylmethane Dyes.” E. Akgün and M. Tunali, Arch. Pharm., 1988,
321, 921.
• “Funktionalisierungen mit Silylenolethern VII.” E. Akgün and M Tunali, Chem. Ztg., 1988, 112, 242.
of 2-Methyl-1,3-dithiolenium Perchlorate with d2-Silylorganyl Synthons.” E. Akgün and M. Tunali, Doga Bilim Dergisi, 1988, A1, 9, 1.
• “Acid Catalyzed Aldyde-Indole Reaction, Synthesis of Indole Dyes.” E. Akgün and M. Tunali, Arch. Pharm., 1988, 321, 9.
• “Zur Reaktion von N, N-Dimethylanilin und Phenol mit Dithiocarbenium-ionen.” E. Akgün and M. Tunali, Chem, Ztg., 1987, 111, 280.
• “The Reaction of Electron-rich Heterocycles with the Derivatives of Carboxylic Ortho Acids VII.” E. Akgün, M. Tunali and U. Pindur, Arch. Pharm., 1987, 320,
397.
• “Functionalization with Silyl Enol Ethers VI.” E. Akgün, M. Tunali and U. Pindur, Monatsh. Chem, 1987, 118, 363.
Tetrafluoroboraten.” U. Pindur, C. Flo, E. Akgün and M. Tunali,. Liebigs Ann. Chem., 1986, 1621. • “Ein einfacher Zugang zu 3-Dithiolanylindolen.” E. Akgün, M. Tunali and U. Pindur, Liebigs Ann. Chem., 1986, 1628. • “BF3-induzierte regioselektive Acylierung von Morpholinoenaminen.” E. Akgün, M. Tunali and U. Pindur, Chem. Ztg., 1986, 110, 335.
• “Reaction of 2-Alkoxy-1,3-dioxolenium-ions with nucleophiles.” E. Akgün and M. Tunali, Doga Bilim Dergisi., 1985, A1, 9, 258.
• “Zinkchlorid-induzierte Alkoxyalkylierung von Trimethylsilylenolethern.” E. Akgün and U. Pindur, Liebigs Ann. Chem., 1985, 2472. • “Synthesewege zu und synthetische Verwendung von 2-Vinylindolen.” E. Akgün and U. Pindur, CHIMIA, 1985, 39, 264.
• “Chemische Eigenschaften und Syntheseverfahren von 3-Vinylindolen.” E. Akgün and U. Pindur, J. Het. Chem., 1985, 22, 585.
• “Zur Konstitution und Konformation von arylsubstituierten(Pyrazolinonyl)- (hydroxypyrazolylium)methanperchloraten.” E. Akgün and U. Pindur, Arch.
Pharm., 1984, 317, 373.
• “Silyl Enol Ethers in Organic Chemistry.” E. Akgün, Doga Bilim Dergisi., 1984,
A1, 8, 124.
• “Synthese von α-und γ-geschützten Dicarbonylverbindungen.” E, Akgün and U. Pindur, Monatsh. Chem., 1984, 115, 587.
• “Eine einfache Synthese von α, β-ungesättigten-γ-geschützten 1, 5- Dicarbonylverbindungen.” E. Akgün and U. Pindur, Synthesis., 1984, 227. • “Reaktivität und Regioselektivität elektrophiler Substitutionen an einfachen Indolen.” U. Pindur and E. Akgün, Chem Ztg., 1984, 108, 371.
• “Zur Reaktion von Phenazon und lithierten Phenazon mit Aryl-Carbonyl- Derivaten.” E. Akgün and U. Pindur., Monatsh. Chem., 1984, 115, 197.
• “Tri-und Tetra-aryl(bzw.-hetaryl)-methane als Pharmaka.”U. Pindur and E. Akgün, Pharm. Uns. Zeit., 1983, 135 • “Blei, Cadmium, Arsen und Thallium in Arzneistoffen, Fertigpräparaten und Drogen.” U. Pindur and E. Akgün, Apotheker Ztg., 1983, 23, 2322.
• “Lewis-Säure-Komplexe des Phenazons.” U. Pindur and E. Akgün, Apotheker Ztg.,1983, 123, 2156.
• “Zum Reaktionsverlauf der Farbreaktionen von Phenazon mit Xanthydrol.” U. Pindur and E. Akgün, Arch. Pharm., 1983, 316 , 89.
• “Reaktionen von elektronenreichen Heterocyclen mit Orthocarbonsäure- derivaten I. E. Akgün U. Pindur, and J. Müller, J. Het. Chem., 1983, 20, 1303.
• “Regiospezifische α-geschützte Acylierung von Silylenolethern.” E. Akgün and U. Pindur, Chem Ztg., 1983, 107, 237.
• “Regiospezifische α-geschützte Formylierung von Silylenolethern.” E. Akgün and U. Pindur, Chem. Ztg., 1983, 107, 236.
• “Blei-und Cadmiumbestimmungen in Arzneimitteln mit der Atomabsorptions spektroskopie.” E. Akgün and U. Pindur, Pharm. Acta Helv., 1983, 58, 130.
• “Zur Struktur von (Pyrazolinonyl)-(hydroxypyrazolylium)methan-perchloraten NMR-,IR-spektroskopische Studien und Kristalstruktur.” Ch. Burschka, E. Akgün
and U. Pindur, Z. Naturforsch., 1983, 38b, 373.
• “Darstellung und Struktur von Pyrazolyl-Kationen mit Polymethin-und Methan- Gerüst.” E, Akgün, T. Kämpchen and U. Pindur, Monatsh. Chem., 1983, 114,
• “Zu säurekatalysierten elektrophilen Substitutionen an 1,2-Dihydro-1, 5-dimethyl- 2-phenyl-3H-pyrazol-3-on (phenazon).” E. Akgün, Chem. Ztg., 1982, 106, 371.
• “Spurenanalyse von Blei, Cadmium und Thallium in Arzneistoffen und zugehörigen Fertigpräparaten mit der Atomabsorptionsspektroskopie.” E. Akgün
and U. Pindur, Pharm. Ind., 1982, 44, 930.
• “Metallation of O-Halostyrene Oxides.” E. Akgün, M. B. Glinski, K. L. Dhawan and T. Durst, J. Org. Chem., 1981, 46, 2730.
• “Stabilisierung von Thioniumcarbenium-Salzindurch +M-Substituenten.” K. Hartke and E. Akgün, Liebigs Ann. Chem., 1981, 47. • “Thiiranium-Salze.”, E. Akgün, K. Hartke and T. Kämpchen, Arch. Pharm., 1980, • “Zur Reaktion von Trichlormethylsulfiden mit Antimonpentachlorid.” K. Hartke and E. Akgün, Chem. Ztg., 1980, 104, 177.
• “Zur Reaktion α-halogenierten Sulfide mit Antimonpentachlorid.” K. Hartke and E. Akgün , Chem. Ber., 1979, 112, 2436.
ABSTRACTS
• “Synthesis of a delta agonist pharmacophore for bivalent ligands”Akgun, E. Symposium on Bivalent Ligands for Opioid Receptors Minneapolis, MN , June 23, 2004 • “ Synthesis of delta-opioid Receptor/alpha2 Adrenoreceptor Bivalent Ligands.” PNI Symposium , Minneapolis, April 16, 2003 SCREENING ASSAYS FOR IDENTIFIYING AND PROFILING ESTROGEN LIGANDS.” Steffend, L.C.; Erwin, K.M.; Ozers, M.S.; Shekhani, M.S.; Akgun, E.; Qadir, N.; Eliason, H.C.; Lowery, R.G.; Burke, T.J. PanVera, 2002, Madison, WI 53719.USA • “N1-(p-[18F]FLUOROBENZYL)NALTRINDOLE (p-[18F]BNTI) AS PET IMAGING AGENT. E. Akgün, M. Sajjad, C.D.Arnett, P.S. Porthoghese, 214th ACS Meeting, Las Vegas, Naveda, September 7-11, 1997: Med. Chem.235 • “Synthesis and use of N1”-(p-fluorobenzyl)naltrindole (FBNTI).” E. Akgün, D. A. Rottenberg, P. S. Portoghese 213th ACS Meeting, San Fransisco, California, April 13-17, 1997: Med. Chem. 238 • "Specific in Vivo Binding of [11C] Naltriben to Delta Opioid Receptors in Mouse Brain." C. D. Arnett, M. Sajjad, E.Akgün, P. S. Portoghese, Society for Neuroscience, 25 th Annual Meeting, San Diago, California, November 11-16, 1995. • "[11C] Naltriben: Synthesis and Biodistribution of a Selective δ2-Opioid Receptor Antagonist for PET Imaging." M. Sajjad, C. D. Arnett, T. T. Conway, E. Akgün, P. S. Portoghese, Eleventh International Symposium on Radiopharmaceutical, Vancouver, B.C., Canada, August, 13-17, 1995 • “F-18 Nucleophilic Substitution Reactions Using Methylsulfone as an Aromatic Activating Group.” C. A. Mathis, E. Akgün, K. Mahmood and N.R. Simpson, the Society of Nuclear Medicine 41st Annual Meeting, Orlando, Florida 1994, Radiopharm. Chem. 1030. • “Asymmetric Synthesis of 4-Aryl and 4-Heteroryl β-lactams. Approaches Toward the Semi-synthesis of Taxol Analogues and A Taxol Metabolite.” H. Park, E. Akgün, Z.S. Cheruvallath, G. C. B. Harrimann, H. Ping, M. Hepperle and G. I. Georg, 1992 ACS Midwest Regional Meeting, Lawrence, Kansas, November 1– • “Enantioselective Synthesis of β-Lactams for the Preparation of C-Taxol Side Chain Analogues.” M. Hepperle, E. Akgün, Z. S. Cheruvallath, G. C. B. Harrimann, H. Ping, H. Park, D. Vander Velde and G. I. Georg, 1992 ACS Midwest Regional Meeting, Lawrence, Kansas, November 1–3, 1992: Org. 507. • “Asymmetric Synthesis of β-Lactams and N-Benzoyl-(2R, 3S)-3-phenylisoserines via the Staudinger Reaction, 201th ACS National Meeting, Atlanta, April 14–19, 1991: Org. 226. • “Stereoselective Synthesis of the Phenylisoserine Side Chain of the Anticancer Agent Taxol.” M. W. Milstead, L. R. Jayasinghe, P. Mashawa, E. Akgün and G. I. Georg, 25th ACS Midwest Regional Meeting, Manhattan, November 8–9, 1990: Org. 165. • “Metal -Directed Stereoselective Synthesis of 3-(1’-Hydroxyethyl)-2-azetidinones, 3-(N,N-Dimetylamino)-2-azetidinones and β-Hydroxy α-amino acids.” G. I. Georg and E. Akgün, 200th ACS National Meeting, Washington, D.C., August 27–31, 1990: Org. 252. • “A Novel Synthesis of 2-Vinylindoles and their Utilization in the Diels-Alder Reaction of New [c] Anellated Carbazole Derivatives.” E. Akgün, M. Tunali and G. Erdönmez, 198th ACS National Meeting, Miami Beach, FL September 10–15, 1989: Org. 48. • “Functionalization with Silyl Enol Ethers, Zinc Chloride Mediated Alkoxyalkylation of (Trimethylsiloxy)alkenones with Cyclic Orthoester Derivatives.” E. Akgün and M. Tunali, 198th ACS National Meeting, Miami Beach, FL September 10–15, 1989: Org. 247. • “Influence of the Metal Ion on the Stereocontrolled Formation of 3-Hydroxyethyl- 2-azetidinones.” E. Akgün and G.I. Georg, 27th Annual Medicinal Chemistry Meeting-in-Miniature, Minneapolis, Minnesota, April 21–23, 1989. • “Preparations of Benzocyclobutanols.” T. Durst, M.B. Glinski, and E. Akgün, 180th ACS National Meeting, San Francisco, California, August 24–29, 1980: Orgn. 154. • “Cyclobutanols and Benzocyclobutanols.” T. Durst and E. Akgün, C.I.C.- • “Preparations of Benzocyclobutanols.” T. Durst, M.B. Glinski, and E. Akgün, 180th ACS National Meeting, San Francisco, California, August 24–29, 1980: Orgn. 154. BOOKS

Akgün, E. “ A review of Phytochemical Research in Turkey” Research Institute for Basic
Sciences, Gebze-Kocaeli, Turkey, 1983; 150 pages.
Akgün, E. “ Analysis of Toxic Heavy Metals and Atomic Absorption Spectroscopy”
Research Institute for Basic Sciences, Gebze-Kocaeli, Turkey, 1983; 100 pages.
Relevance to Pharmacy Education:

During my training, I was a teaching assistant in organic chemistry and supervised the
analytical chemistry laboratory for medical students for two years (1975-1977). I was
also a teaching and laboratory assistant in quantitative analysis for pharmacy students.
My duties were: Preparation and Dispensing of analysis, teaching relevance material
and testing the student orally, and grade their written exams. The analysis consisted of
gravimetric, potentiometer, palarography, and spectroscopic analysis for three years
(1977-1980). As graduate student, I was actively involved in the organic chemistry seminar program. I presented several seminars and was also involved in guiding pharmacy graduate students in their preparation for the graduate seminar in organic chemistry. Having been a teaching assistant for five years provided me with the opportunity of close interaction with undergraduate students. I really enjoyed teaching these students in seminars and in the laboratory. I tried to make sure that they understood the underlying theoretical chemical principles before they started their work in the laboratory. I placed particular emphasis on developing their thinking abilities. I found it very satisfying to share my knowledge and to teach the students to perform the experiments with care and accuracy. I was involved in conducting oral examinations with students and graded their manuals and exams. After my Ph.D. thesis defense, I got a project from German ministry of health and Family to study the toxic heavy metals in drugs and prodrugs with atomic absorption spectroscopy. These include the technique such as flame, graphite, and hybrid technique. In united state I learned to analyze radioactive materials and their synthesis for positron emission tomography. I am very experienced modern organic chemistry analytic technique such as NMR spectroscopy and teaching the variety of these techniques and maintain the instruments. In my organic chemistry analytic methods I investigated variety of drugs analytically for their indole and phenazone (antipyrine) contents. The publications belong to this area are summarized as follows: • “Blei, Cadmium, Arsen und Thallium in Arzneistoffen, Fertigpräparaten und Drogen.” U. Pindur and E. Akgün, Apotheker Ztg., 1983, 23, 2322.
• “Lewis-Säure-Komplexe des Phenazons.” U. Pindur and E. Akgün, Apotheker Ztg.,1983, 123, 2156.
• “Zum Reaktionsverlauf der Farbreaktionen von Phenazon mit Xanthydrol.” U. Pindur and E. Akgün, Arch. Pharm., 1983, 316 , 89.
• “Spurenanalyse von Blei, Cadmium und Thallium in Arzneistoffen und zugehörigen Fertigpräparaten mit der Atomabsorptionsspektroskopie.” E. Akgün
and U. Pindur, Pharm. Ind., 1982, 44, 930.
• Gerüst.” E, Akgün, T. Kämpchen and U. Pindur, Monatsh. Chem., 1983, 114,
• “Zu säurekatalysierten elektrophilen Substitutionen an 1,2-Dihydro-1, 5-dimethyl- 2-phenyl-3H-pyrazol-3-on (phenazon).” E. Akgün, Chem. Ztg., 1982, 106, 371
Diindolylantipyrylmethane Dyes.” E. Akgün and M. Tunali, Arch. Pharm., 1988,
321, 921.
• Akgün, E. “ Analysis of Toxic Heavy Metals and Atomic Absorption Spectroscopy” Research Institute for Basic Sciences, Gebze-Kocaeli, Turkey, 1983; 100 pages.

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